Dan's Mom Substitutes For DaughterbyJRob©
It's hard being a senior in high school, especially when your older brother was a sports icon. Many think it would be easier, but let me tell you, it is anything but.
The coaches think you have sports talent, but I didn't. The teachers think you can replicate his book knowledge, I can't. And the girls that flocked to his side, well, their younger sisters would have nothing to do with me.
It's not fair, but it was reality.
My best friend Dan and I would discuss everything and anything. We'd double dated a couple times, and he even tried to get me a date with his sister but she'd have nothing of it. On those hot days, I was joined in my bedroom by Dan to spy on the girls who loved sitting out by their pool and soaking up rays.
Sometimes their tops would come off, but hardly ever in a way that we got more than a glimpse of breast. It's like they had special antenna that went up when we were watching.
When we were lucky enough to hit the jackpot, and get a view of perky teenage tits, we both not only smiled but grimaced. They were so beautiful. To be honest, I had fondled Lisa Gentry's boobs both over and under her top, but had never really saw them with anything other than my hands. Dan did admit to seeing, and licking, Mary Bartholomew's boobies on several occasions before they broke up.
Still watching Jennifer, his sister, or friends Courtney and Amber, bare their 18-year-old boobs on those infrequent occasions was quite the erotic treat.
There was a warm Tuesday when I was home early from school where I got a special treat. Dan's mom was out back, sunning, wearing only a bikini bottom. Her large breasts were fully on display when I peeked out of my window.
At first I was shocked, but my brain told me the 40-something woman deserved an all-over tan as much as her daughter. I stared at her, lust in my brain, for more than a half hour. That night I jerked off thinking about the MILF, she replaced her daughter as the focus of my nocturnal ministrations for the next several weeks.
Oh, I still thought of Dan's sister Jennifer in my late night activities, and once even had the two of them in a three-way tryst. Ah, the mind can really expand when women are in the middle of things.
I finally did get a date with Jennifer, a couple of weeks after she broke up with a blowhard full of himself guy named Bill. It was a sort of, well, mercy date. Dan convinced her it was good to get out on dates, and she really wasn't over Bill. So I became the perfect stand-in, just like in the movies where the star doesn't do the stunts, his double does.
We went to Sonic for burgers the first time, and it actually was fun. She gave me a good night peck on the cheek that I rubbed in and later rubbed off to. Our second date was to the movies, were I conveniently put my arm around her to hold her close during the scary scenes.
That night I dropped her off, getting a nice smooch on the lips. I tried for a little tongue, but there was an iron wall there and my lips never got past the gate.
During the week I'd attempt to spy on the girl and her mom when she sunbathed, never catching bared breasts but still loving every nook and cranny I could see. She'd lower her bikini bottom a little for more sun, and I loved the new (to my eyes) inch it displayed.
That looking got me in trouble, though, as the next afternoon Mrs. Johnson, Dan and Jennifer's mom, smiled at me and said hi on my way home from school.
"Where's Danny," asked his mom.
"Oh, he was staying behind today to ask the science teacher some questions on his quarterly project."
Her smile changed to a sort of grimace. "So, Rob, did you enjoy the view yesterday?"
My mind had no idea of what to say.
"Go ahead, admit it, you were spying on us, weren't you," said the inquisitor mom from next door.
Stuttering something or another, Mrs. Johnson shushed me.
"Look Rob, you aren't going to be allowed to go out with Jennifer again if you don't answer the question honestly. Were you being a little voyeur up in your room yesterday?"
We stared at each other for a minute before I answered in the affirmative.
"And you think that's a normal thing to do, spy on women from your room. What else have you looked at? Have you looked into Mr. Johnson and me in our bedroom? Have you looked up our skirts at the mall? Have you snuck in and jerked off on our panties?"
My eyes widened at the question, and I quickly said no, no nothing like that.
"Like what then?" demanded the woman.
"Nothing Mrs. Johnson, honest, I just looked out my window at you two sunbathing, I didn't mean anything by it. I mean, it was an accident and my mind started wandering and I couldn't stop looking. Please don't tell Jennifer, or my parents, Please."
She looked at me, as if to judge my sincerity. She nodded her head.
"So did you see what you wanted to see? Did you whack off at night after you looked at Jennifer? Is that where your mind was wandering?"
I didn't know what to say, but Mrs. Johnson told me to be honest or else. So I admitted that it was a great view, that I looked at Jennifer's boobs, and admitted to looking at hers as well. And I admitted I had jerked off thinking about them as well.
She should have been a prosecuting attorney. She pounced and bounced along everything I said, switching topics with her technique.
"So have you made out with my daughter, felt her up? Did you sleep with her?"
I quickly replied "NO."
Mrs. Johnson smiled a little and then nodded. "But you want to, right?"
Of course I did, what normal guy wouldn't. I explained that I would never take advantage of her daughter and would treat her with respect.
"But you would feel those breasts if she let you, right? You'd still sleep with her if you could. I mean if she said she'd give you a blow job you wouldn't turn her down, now, would you."
Damn, how do I answer those questions. Damned if I did, damned if I didn't. Luckily, my mom's car pulled into the driveway and I earned a reprieve.
"We are not done this conversation yet, buster, and you had better keep your hands to yourself when you are out with my daughter, do you understand? Do you? Otherwise there will be hell to pay."
@ @ @ @ @
It was a tough night. I had been busted by my sort of girlfriend's mom, the mother of my best friend and of course my neighbor. She had said all kinds of things that I had been dreaming about. I thought of Jennifer's boobs, and that night I pretended she was going down to me at the end of a date. Damn, my sock got filled with sticky stuff that night.
Jennifer was none the wiser that weekend. We went to a party, and on the way home she informed me that she was going out with Ryan the next night. She wanted me to know, her mother insisted I was told, so that I didn't think she was going out behind my back.
We weren't going steady, or anything, but I had to wonder if her mother had said something to her to incent her to see someone else and not the pervert next door.
Peeved, I understood the girl's decision. I did ask for a date the following weekend and she smiled, said of course, and kissed me good night, this time with a little peek of tongue.
I guess all 18-year-old guys whack off a lot. I know I did, and my friends who weren't getting laid did as well. Dan admitted he whacked off four or five times a week, just about the same as I did. I mean, we were guys you know.
The following night I watched from upstairs when Ryan brought Jennifer home, and for a first date there was more than a pack on the cheek. They kissed for a full minute and I was very jealous.
Monday afternoon I was again stopped my Mrs. Johnson on my way home from school. "So, do you want to finish our conversation?"
Reluctantly I did, admitting that I thought naughty thoughts about her daughter. "And what about me?"
I admitted it. I said I had thought of her at night, doing bad things. Being a bad girl.
"Even thought I am the same age as your mother."
I nodded yes. I said she was beautiful, that she was so very hot and sexy too. I figured if I were honest she'd be assured I wouldn't be anything but proper with her daughter.
"Okay, Rob, I trust you, and I know you won't do anything to break that trust, right? Jennifer has quite a head on her, and we want her to go to college and do well there. We don't want her head going boy-crazy. We had to break her and Ryan up the other night on the porch."
She made good points. Jennifer was the smartest girl in our class and had a scholarship to State U. That had to be important to the girl and her family.
Like before, Mrs. Johnson shocked me a little with her next question. "Are you a virgin, Rob?" After I nodded yes, she asked, "what kind of naughty things did you do to me in your nighttime fantasies? Be honest or else."
Again, it was as if I had ingested some truth serum. All came out.
"I, uh, well, I thought of you doing some bad things with me. I thought of you stripping down to your underwear for me."
"Oh you did, did you? What else?"
"Blow job. I, uh, I thought of you giving me a blow job and then bending over the kitchen counter where we had sex. There, I said it, please don't be mad at me, it was only a fantasy."
The women spoke about my active mind, and how I was very, very naughty. "I don't know, but if I thought your mother would have your dad use the belt on you I would."
We looked at each other for a bit before she smiled. "Those are naughty thoughts, but I bet Dan thinks the same way about girls. So let's forget we had this conversation and just make sure you treat my daughter well."
That night I had naughty thoughts about my best friend's mom. The following day I saw her, and she asked if I could stop by the next afternoon. "I have a couple things I want you to around the house and Dan is working on the play and Mr. Johnson is away for the rest of the week."
Of course I said yes, I'd done some things for her in the past and saw this as a good idea to make sure all was good between us.
@ @ @ @ @ @
The next afternoon I spent an hour fixing a broken bannister to the attic. There was nothing too hard, just a nuisance to fix. I had to Rube up a makeshift fix, but it worked and Mrs. Johnson was genuinely appreciative.
We shared a diet coke and made chit chat for a couple minutes, and she gave me a $20 bill for my work. She asked if I was taking her daughter out that weekend and I nodded in the affirmative.
"You won't be back before 11 will you?" asked the woman.
My first thought was yes, but I thought and said the movie started at 8:30 so we'd probably stop for cokes after, so 11 was pushing it.
"Well just make sure before midnight, but not before 11 okay?"
My look must have had a question on it.
"Well, Mr. Johnson is getting back from his business trip Saturday night and I was, well, hoping we'd have a little, uh, quiet time together with the kids out of the house. Jennifer will be with you, and Dan has a date with Trisha. So I was hoping...."
"Guarantee we won't be home before 11:15 Mrs. Johnson," was all I could muster up. "Not a problem. We will come home after the movie and won't be driving fast."
Then the woman surprised me. "I have two outfits I'm considering wearing. Would you give me a man's opinion?"
That was a no—brainer, of course.
With that the women sped upstairs and I waited in the living room. I wondered if it would be a little black dress, or a red one. Maybe a sexy skirt and tight top? She didn't really say where they were going.
Boy was I wrong.
The first outfit was a baby blue, baby doll nightie. She looked adorable. Once I was over the shock of seeing the outfit that left little to the imagination, I said it was perfect. It looked great on her.
She walked back upstairs and I could not help watching her panty clad buns walk. It was so hot, and I wondered what would be next. I just hoped it would be more lingerie. It was.
Her second outfit was a short black night dress, accentuated by black stockings. When she twirled around she hem rose and I saw both stocking tops, garters and black panties. Wow.
So I told her. "Wow, that's an unbelievably sexy outfit."
She asked if it was really sexy enough, and I said something about a blind man would fall in love with the way she looked in it.
"You are so nice, thanks for the feedback," she said, reminding me to shut the door tightly on my way out. That night guess who was the object of my affections, and what she was wearing?
@ @ @ @ @ @
The following weekend my date with Jennifer was wonderful. We went to an upscale burger joint, then a movie. On the way back to her house I stopped at a local park and we kissed for a couple minutes until the cops chased us.
Looking back I guess we should have been more embarrassed or something. But on the other hand, we weren't really doing anything. Just talking with a few kisses thrown in. Truthfully, I just didn't want to mess up the timing her mother had outlined.
We arrived at her house a little after 11:30 and kissed in the car for a couple minutes. Jennifer is such a good kisser, using not only her lips but when she used tongue my mind wandered to other places I'd like it to explore.
We walked, hand in hand, to her front door, kissed again, and I said goodnight with a big smile on my face. On the way home I thought about her parents and what they probably were doing while we were on the date.
Whether they did the nasty or not, that night I used it as my fantasy while I was whacking off. I thought of the positions Mr. J was putting his wife, and how they were enjoying themselves. Needless to say I didn't last long.
A couple days went past before Mrs. Johnson corralled me on the way home. I was walking, about four blocks from home, when she invited me into her call. She was all gussied up and looked great.
"Made a great sale today, a house over on Elm, it was great," said the woman her skirt riding high enough for me to see her stocking tops.
"Caught you," said that woman, catching my look. She smiled and let out a little laugh. "Were you looking at these?" With that she slipped up her skirt a couple inches, showing the stocking tops and milky white legs above. "Now be a gentleman and look the other way," she said, smoothing down her skirt.
We got home and she asked how things had gone with Jennifer Saturday night. "Did you have fun...did you kiss her?"
I said yes to both, thanking her for trusting me with her daughter. Once again I said we weren't getting too serious, that I really liked being with her daughter.
"You have that look in your eye, that I'm saying one thing but going to do another look," said the women. "I can read guys like a book. You want to bang my daughter, don't you."
I can't believe how Mrs. Johnson always knew what was on my mind. Without thinking, I blurted out "of course" before quickly looking away in embarrassment.
Mrs. Johnson was quiet for a few seconds and then rebounded back to the topic at hand. She reminded me that Jennifer was a virgin, that she wanted her to stay that way and concentrate on school books not guys.
"We've got a problem here. You want sex, she is holding you off, but each date it gets harder and you get harder, so to speak, and more persuasive. That's not going to work."
Jennifer's mom said once again that accidents happen, girls get pregnant, and careers are detailed. She did not want that for her daughter. She wanted a strong education completed before, as she said it, major hanky panky occurred.
We arrived home and she asked me into the house. We sat and talked, sharing soft drinks.
"Jennifer really likes you. Who knows what will happen down the road but she likes you. And I like you too, you're a nice guy with a great head on your shoulders and personality. You are a good catch, but it's not the time for getting serious."
We stared at each other.
"What's it going to take to keep you out of her pants?" said Mrs. Johnson? "I guess we could break you two up, but that would probably bring you too together. Maybe if you found another girl to take care of your needs....I hear Danielle Dawkins is pretty easy."
I laughed. Danielle was known by many of the guys as the school cum dump. At least that was the rumor. She'd date guys for a couple weeks tops, and supposedly had sex with them. Sort of another notch on her lipstick case, and that case came in various colors.
Once or twice I'd asked her out, hoping to get some of that stuff she was giving out, but she shooed me away. There was always a sports star that caught her attention.
Jen's mom was obviously concerned. It was as if she had been there before, which obviously she had. But maybe something happened in her teen years that made an impact. Or, more likely, she just knew guys liked to get into girl's pants. Go figure!
"I will try to, you know, hold off with your daughter. I mean, I respect her and admire her. She is very sexy, but I can try..."
The room because oh so quiet. Mrs. Johnson looked at me, I at her. My girlfriend's mom totally surprised me with what she said next. "What if you had some incentive?"
I must have looked as if she was speaking another language.
"Let me spell it out for you, Rob,, what if you were getting some, you know, sex, elsewhere. Would you keep your hands out of Jennifer's pants? Well, would you."
"But I don't want to break up with her, Mrs. Johnson, I really like her."
The woman explained she didn't want us to break up, only have my manly needs as she called it handled elsewhere. In return, Jennifer would remain as pure as a morning snow.
Mrs. Johnson stood, walked over and sat down next to me on the couch. Looking in my eyes, she reached down and grabbed my hand. If you had incentive not to sleep with her, could you make sure you kept it in your pants when you went out with her?"
My immediate through was dread, then a smile crossed my face. "You mean..."
Mrs. Johnson smiled back. "I think you are catching on, but the real question is whether you can keep a secret. Whether you can keep to yourself whatever happens. Not saying a word to a friend or enemy."
Merely saying "of course, absolutely" was apparently the right answer.
"I mean it, not to your best friend or anyone for that matter. Nobody knows about this right?"
I merely nodded and with that my girlfriend's mom began stroking my cock through my pants. Soon a tent appeared.
"I think he likes me, but the question is, does he like me more than me likes my daughter?"
The feeling on my dick was incredulous, the stroking was so very hot. Soon the woman was unzipping my fly. She reached into my briefs and found an exit strategy for my rock hard cock. She kept stroking while she asked if I'd stay away from Jennifer's pants.
"No sex with her, young man. But I know you are a man and have needs. I could supply those needs if you stay away from my daughter's pussy."
Hearing those words sparked my dick to more attention, and her stroking was so very hot. I couldn't help myself. I started erupting in her hand. Mrs. Johnson didn't back off, she kept stroking my dick while kissing my neck. "You have a great cock," she cooed. "Stay away from my daughter's snatch and I can make you very, very happy."
She kept stroking my dick, as all my sauce spilled out. The first few globs were spurted, but at the end there were just dribbles that ended up as more lubrication as she stroked me. I lay back in another world as she asked again if we had a deal.
"We have a deal, Mrs. Johnson, we have a deal."
She smiled a knowing smile.